EP0707580A1 - Omeprazole de magnesium - Google Patents

Omeprazole de magnesium

Info

Publication number
EP0707580A1
EP0707580A1 EP94921154A EP94921154A EP0707580A1 EP 0707580 A1 EP0707580 A1 EP 0707580A1 EP 94921154 A EP94921154 A EP 94921154A EP 94921154 A EP94921154 A EP 94921154A EP 0707580 A1 EP0707580 A1 EP 0707580A1
Authority
EP
European Patent Office
Prior art keywords
magnesium omeprazole
magnesium
omeprazole
determined
crystals
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP94921154A
Other languages
German (de)
English (en)
Other versions
EP0707580B1 (fr
Inventor
Lars Ake KÄLLSTRÖM
Monica Annelie Nygren
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AstraZeneca AB
Original Assignee
Astra AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20390588&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0707580(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Astra AB filed Critical Astra AB
Priority to SI9430414T priority Critical patent/SI0707580T1/xx
Priority to EP01117362A priority patent/EP1164132A3/fr
Publication of EP0707580A1 publication Critical patent/EP0707580A1/fr
Application granted granted Critical
Publication of EP0707580B1 publication Critical patent/EP0707580B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the present invention relates to a novel process for manufacturing the magnesium salt of omeprazole; the magnesium salt of omeprazole in a novel physical form, especially the magnesium salt as a product of the novel process; the use of the novel form of the magnesium salt of omeprazole in the manufacture of pharmaceutical formulations; and to the use of the novel form of the magnesium salt of omeprazole in medicine.
  • Omeprazole is useful for inhibiting gastric acid secretion and has gastric mucosa protective activity in mammals and man.
  • omeprazole may be used for prevention and treatment of gastric a- .d related disorders and gastrointestinal inflammatory diseases in mammal and man, including e.g. gastritis, gastric ulcer and duodenal ulcer.
  • omeprazole designates the neutral form of the compound, that is the form without a salt forming cation present.
  • magnesium omeprazole salts are very fragile making processes utilising such crystals less attractive in full scale production. Performing the process without crystallization of the magnesium omeprazole gives a product which is less suitable as a pharmaceutical substance.
  • magnesium omeprazole in this specification denoted magnesium omeprazole
  • One object of the present invention is to provide a process for full scale production of magnesium omeprazole.
  • a further object of the present invention is to provide a novel form of the magnesium salt of omeprazole which can be used in full scale manufacturing of pharmaceutical formulations, such as tablets.
  • the combination of physical properties of the novel magnesium omeprazole product of the present invention with respect to the degree of crystallinity, particle diameter, density, hygroscopicity, water content and content of other solvents are favorable and permit the manufacture of magnesium omeprazole in a form which possesses the desired properties.
  • novel form of magnesium omeprazole can also be formulated into other forms for oral administration and other types of administration such as rectal administration.
  • examples of formulations are tablets, pellets, granules, capsules, suspensions and suppositories.
  • the novel process for the manufacture of magnesium omeprazole also circumvents the above described manufacturing problems and renders possible the recovery and work-up of the magnesium omeprazole substance in traditional chemical process equipment.
  • MMD mean mass diameter
  • the invention also relates to a process for manufacturing the novel form of magnesium omeprazole. This process is described in more detail below.
  • the invention relates to all of the aspects given under Field of the invention.
  • a lower alcohol such as methanol, ethanol, n-propanol or iso-propanol, preferably methanol
  • a solution of polar solvents with a weighed amount of magnesium at temperatures between 0°C and reflux temperature.
  • the temperature should preferably be between 10 and 30°C.
  • the temperature can, in a second step be raised further to between 0°C and reflux temperature, preferably 20-50°C.
  • the temperature is reduced to 0-40°C, preferably 10-25°C.
  • Omeprazole or a salt of omeprazole is then added to the solution and after termination of the reaction the mixture is cooled to -10°C to +20°C, preferably -5°C to +5°C.
  • the solvent is then evaporated to 40-60% of the initial volume, which makes the inorganic salts precipitate.
  • the precipitate is separated from the reaction solution for example by centrifugation or filtration and the solution is heated to 5°C to 30°C whereafter the solution is seeded with magnesium omeprazole crystals.
  • An amount of water which is approximately equal to the volume of the solution, is added to start the crystallization.
  • the solution is cooled to -10 to +20°C, preferably 0-10°C to complete the crystallization.
  • the crystals are then separated from the mother liquid for example by centrifugation or filtration and washed with polar solvents preferably an aqueous lower alcohol such as aqueous methanol. Finally, the produced crystals are dried preferably under reduced pressure and heating.
  • the process for manufacturing the new form of magnesium omeprazole differs from the earlier known processes in that the product is recovered after a controlled crystallization step in aqueous alcohol, preferably methanol by, first, separating the inorganic salts from the mother liquour.
  • the crystallinity resulting from this step is, unexpectedly, higher and the product possesses a higher degree of purity and is more stable to decomposition from uptake of moisture.
  • the drying step can be performed without caking.
  • the new process is possible to perform in conventional chemical process equipment and gives a product with a higher yield than the processes hitherto known.
  • Example 1 The following detailed Example 1 will serve to more fully illustrate the process for manufacturing magnesium omeprazole in full scale according to the present invention.
  • sample A is manufactured according to this example.
  • a reactor was filled with 2026 litres of methanol. The stirrer was started and the temperature was adjusted to 20°C. 3,90 kg of magnesium was added to the vessel and immediately thereafter 1,0 litre of Cr ⁇ Ck,. The reactor was heated to 40°C and kept at this temperature for 60 min. It was then cooled to 15°C before the addition of 99,9 kg of omeprazole. The reactor was kept at this temperature for 60 min and then cooled to 0°C. The temperature was kept at this level for 30 minutes before 1000 1 of methanol were evaporated under vacuum and the inorganic solid salt was separated from the liquid first by centrifugation and then by filtration.
  • the liquid was heated to 10°C and the liquid was seeded with magnesium omeprazole crystals whereafter the magnesium omeprazole salt was precipitated by addition of 900 1 of water.
  • the mixture was then cooled to 5°C. After the crystallization had been completed the magnesium omeprazole crystals were centrifuged off and then washed with a mixture of 50 1 of methanol and 150 1 of water.
  • the produced magnesium omeprazole was dried under reduced pressure finally producing 92,5 kg of crystalline product corresponding to a yield of 81,4%.
  • the novel form of the magnesium salt of omeprazole according to Example 1 possesses the following properties:
  • FIG. 1 A comparison between two different samples of the novel form of magnesium omeprazole of the present invention obtained from two laboratory scale experiments by prior art methods and magnesium omeprazole goes forth from diagrams 1 and 2.
  • sample A represents the novel form of the present invention as manufactured in full scale process equipment
  • Sample B represents the product of preparation via synthesis by treatment of omeprazole with Mg(OCHg)2-
  • Sample C represents the product of preparation via treatment of sodium omeprazole with MgC ⁇ .
  • Figure 1 shows in diagram 1 that the particle size measured as mean mass diameter of the product of method A is 19 ⁇ m which is smaller than the corresponding particle size for the products of method B which is 25 ⁇ m and of method C which is greater than 600 ⁇ m.
  • Figure 2 shows in diagram 2 that the degree of crystallinity of the particles of the product of method A is 76% which is higher than the corresponding figure for the product of sample B, which is 0% and also higher than the corresponding figure of sample C, which 67%. '

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroplating Methods And Accessories (AREA)
  • Conductive Materials (AREA)
  • Contacts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Powder Metallurgy (AREA)
  • Glass Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une nouvelle forme de composé à l'oméprazole de magnésium utilisé dans la préparation de formules pharmaceutiques, l'utilisation dudit produit et son procédé de production.
EP94921154A 1993-07-09 1994-07-08 Omeprazole de magnesium Expired - Lifetime EP0707580B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
SI9430414T SI0707580T1 (en) 1993-07-09 1994-07-08 Magnesium omeprazole
EP01117362A EP1164132A3 (fr) 1993-07-09 1994-07-08 Omeprazole de magnésium cristallin

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE19939302396A SE9302396D0 (sv) 1993-07-09 1993-07-09 A novel compound form
SE9302396 1993-07-09
PCT/SE1994/000680 WO1995001977A1 (fr) 1993-07-09 1994-07-08 Omeprazole de magnesium

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP01117362A Division EP1164132A3 (fr) 1993-07-09 1994-07-08 Omeprazole de magnésium cristallin

Publications (2)

Publication Number Publication Date
EP0707580A1 true EP0707580A1 (fr) 1996-04-24
EP0707580B1 EP0707580B1 (fr) 2002-01-30

Family

ID=20390588

Family Applications (2)

Application Number Title Priority Date Filing Date
EP01117362A Withdrawn EP1164132A3 (fr) 1993-07-09 1994-07-08 Omeprazole de magnésium cristallin
EP94921154A Expired - Lifetime EP0707580B1 (fr) 1993-07-09 1994-07-08 Omeprazole de magnesium

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP01117362A Withdrawn EP1164132A3 (fr) 1993-07-09 1994-07-08 Omeprazole de magnésium cristallin

Country Status (41)

Country Link
US (1) US5900424A (fr)
EP (2) EP1164132A3 (fr)
JP (2) JP3635432B2 (fr)
KR (1) KR100353783B1 (fr)
CN (1) CN1064680C (fr)
AT (1) ATE212628T1 (fr)
AU (1) AU679766B2 (fr)
BR (1) BR9406940A (fr)
CA (1) CA2166794C (fr)
CZ (1) CZ288933B6 (fr)
DE (2) DE707580T1 (fr)
DK (1) DK0707580T3 (fr)
DZ (1) DZ1792A1 (fr)
EE (1) EE03127B1 (fr)
EG (1) EG21437A (fr)
ES (1) ES2100136T3 (fr)
FI (1) FI114154B (fr)
GR (1) GR970300015T1 (fr)
HR (1) HRP940385B1 (fr)
HU (1) HU226861B1 (fr)
IL (1) IL110190A (fr)
IS (1) IS2075B (fr)
MA (1) MA23257A1 (fr)
MX (1) MX9405217A (fr)
MY (1) MY113274A (fr)
NO (1) NO308702B1 (fr)
NZ (1) NZ268693A (fr)
PL (1) PL175999B1 (fr)
PT (1) PT707580E (fr)
RU (1) RU2139868C1 (fr)
SA (1) SA94150058B1 (fr)
SE (1) SE9302396D0 (fr)
SG (1) SG52464A1 (fr)
SI (1) SI0707580T1 (fr)
SK (1) SK281230B6 (fr)
TN (1) TNSN94079A1 (fr)
TW (1) TW504509B (fr)
UA (1) UA43343C2 (fr)
WO (1) WO1995001977A1 (fr)
YU (1) YU49193B (fr)
ZA (1) ZA944933B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1801110A1 (fr) 2005-12-22 2007-06-27 KRKA, tovarna zdravil, d.d., Novo mesto Sel d'arginine d'ésoméprazole

Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6875872B1 (en) 1993-05-28 2005-04-05 Astrazeneca Compounds
SE9301830D0 (sv) * 1993-05-28 1993-05-28 Ab Astra New compounds
SE9302395D0 (sv) * 1993-07-09 1993-07-09 Ab Astra New pharmaceutical formulation
SE9302396D0 (sv) * 1993-07-09 1993-07-09 Ab Astra A novel compound form
MX9600857A (es) 1994-07-08 1997-06-28 Astra Ab Forma de dosificacion i en tabletas, con unidades multiples.
FI970058L (fi) * 1994-07-08 1997-01-07 Astra Ab Uusi suun kautta annettava farmaseuttinen valmiste, joka sisältää omepratsolin magnesiumsuolaa
SE9500478D0 (sv) * 1995-02-09 1995-02-09 Astra Ab New pharmaceutical formulation and process
US6489346B1 (en) 1996-01-04 2002-12-03 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
US6699885B2 (en) * 1996-01-04 2004-03-02 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and methods of using same
US6645988B2 (en) 1996-01-04 2003-11-11 Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
US5840737A (en) 1996-01-04 1998-11-24 The Curators Of The University Of Missouri Omeprazole solution and method for using same
SE9600070D0 (sv) 1996-01-08 1996-01-08 Astra Ab New oral pharmaceutical dosage forms
SE508669C2 (sv) * 1996-04-26 1998-10-26 Astra Ab Nytt förfarande
US6623759B2 (en) 1996-06-28 2003-09-23 Astrazeneca Ab Stable drug form for oral administration with benzimidazole derivatives as active ingredient and process for the preparation thereof
TW385306B (en) * 1996-11-14 2000-03-21 Takeda Chemical Industries Ltd Method for producing crystals of benzimidazole derivatives
SE510666C2 (sv) * 1996-12-20 1999-06-14 Astra Ab Nya Kristallmodifikationer
SE9702000D0 (sv) * 1997-05-28 1997-05-28 Astra Ab New pharmaceutical formulation
SE510650C2 (sv) 1997-05-30 1999-06-14 Astra Ab Ny förening
US6747155B2 (en) 1997-05-30 2004-06-08 Astrazeneca Ab Process
US6096340A (en) * 1997-11-14 2000-08-01 Andrx Pharmaceuticals, Inc. Omeprazole formulation
US6174548B1 (en) 1998-08-28 2001-01-16 Andrx Pharmaceuticals, Inc. Omeprazole formulation
SE9704870D0 (sv) 1997-12-22 1997-12-22 Astra Ab New pharmaceutical formulation I
FR2774288B1 (fr) * 1998-01-30 2001-09-07 Ethypharm Sa Microgranules d'omeprazole gastroproteges, procede d'obtention et preparations pharmaceutiques
US6048981A (en) * 1998-04-22 2000-04-11 Torcan Chemical Ltd. Magnesium omeprazole and process for its preparation
DE19843413C1 (de) 1998-08-18 2000-03-30 Byk Gulden Lomberg Chem Fab Neue Salzform von Pantoprazol
US6733778B1 (en) 1999-08-27 2004-05-11 Andrx Pharmaceuticals, Inc. Omeprazole formulation
SE9803772D0 (sv) 1998-11-05 1998-11-05 Astra Ab Pharmaceutical formulation
UA72748C2 (en) * 1998-11-10 2005-04-15 Astrazeneca Ab A novel crystalline form of omeprazole
IL142703A (en) * 1998-11-10 2006-04-10 Astrazeneca Ab Crystalline form of omeprazole
EP1131316B1 (fr) * 1998-11-18 2004-07-21 AstraZeneca AB Procede chimique ameliore, et formulation pharmaceutique
TWI243672B (en) 1999-06-01 2005-11-21 Astrazeneca Ab New use of compounds as antibacterial agents
US6316020B1 (en) * 1999-08-26 2001-11-13 Robert R. Whittle Pharmaceutical formulations
SE9903831D0 (sv) * 1999-10-22 1999-10-22 Astra Ab Formulation of substituted benzimidazoles
CA2290893C (fr) * 1999-11-16 2007-05-01 Bernard Charles Sherman Omeprazole de magnesium
DE19959419A1 (de) * 1999-12-09 2001-06-21 Ratiopharm Gmbh Stabile galenische Zubereitungen umfassend ein Benzimidazol und Verfahren zu ihrer Herstellung
SE0000774D0 (sv) 2000-03-08 2000-03-08 Astrazeneca Ab New formulation
AU5248601A (en) * 2000-05-15 2001-11-26 Ranbaxy Laboratories Limited Novel amorphous form of omeprazole salts
CA2386716C (fr) * 2002-05-17 2012-07-24 Bernard Charles Sherman Sel de magnesium de s-omeprazole
AU2001276721A1 (en) 2000-08-04 2002-02-18 Takeda Chemical Industries Ltd. Salts of benzimidazole compound and use thereof
US6544556B1 (en) 2000-09-11 2003-04-08 Andrx Corporation Pharmaceutical formulations containing a non-steroidal antiinflammatory drug and a proton pump inhibitor
WO2002026210A2 (fr) * 2000-09-29 2002-04-04 Geneva Pharmaceuticals Inc. Formulation d'inhibiteur de la pompe à protons
SE0101379D0 (sv) 2001-04-18 2001-04-18 Diabact Ab Komposition som hämmar utsöndring av magsyra
US8206741B2 (en) 2001-06-01 2012-06-26 Pozen Inc. Pharmaceutical compositions for the coordinated delivery of NSAIDs
SE0102993D0 (sv) 2001-09-07 2001-09-07 Astrazeneca Ab New self emulsifying drug delivery system
CA2472103A1 (fr) * 2002-01-25 2003-08-07 Santarus, Inc. Administration par voie muqueuse d'inhibiteurs de la pompe a protons
FR2836228B1 (fr) * 2002-02-21 2005-08-19 Inst Francais Du Petrole Methode et dispositif pour evaluer des parametres physiques d'un gisement souterrain a partir de debris de roche qui y sont preleves
US20030228363A1 (en) * 2002-06-07 2003-12-11 Patel Mahendra R. Stabilized pharmaceutical compositons containing benzimidazole compounds
SE0203065D0 (sv) 2002-10-16 2002-10-16 Diabact Ab Gastric acid secretion inhibiting composition
WO2004073654A2 (fr) * 2003-02-20 2004-09-02 Santarus, Inc. Liberation immediate d'un complexe antacide d'omeprazole presentant une nouvelle formulation pour une elimination rapide et prolongee d'acide gastrique
CN1842525A (zh) * 2003-05-05 2006-10-04 兰贝克赛实验室有限公司 苯并咪唑衍生物的钡盐
US8993599B2 (en) * 2003-07-18 2015-03-31 Santarus, Inc. Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
US20050037070A1 (en) * 2003-07-18 2005-02-17 Santarus, Inc. Pharmaceutical formulatins useful for inhibiting acid secretion and methods for making and using them
CA2531566C (fr) * 2003-07-18 2013-05-07 Santarus, Inc. Formulation pharmaceutique et procede de traitement de troubles gastro-intestinaux lies a l'acidite
WO2005072079A2 (fr) 2003-09-26 2005-08-11 Alza Coporation Enrobage de medicaments a charge medicamenteuse elevee et procedes de fabrication
RU2257890C2 (ru) * 2003-10-06 2005-08-10 Марио Атилио Лос Способ получения устойчивых фармацевтических композиций в форме таблеток, содержащих омепразол, и фармацевтические композиции, полученные таким способом
WO2005082888A1 (fr) * 2004-03-01 2005-09-09 Milen Merkez Ilac Endustrisi A.S. Procede de preparation d'un sel magnesique d'omeprazole
US8815916B2 (en) * 2004-05-25 2014-08-26 Santarus, Inc. Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
US8906940B2 (en) * 2004-05-25 2014-12-09 Santarus, Inc. Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
ES2246149B1 (es) 2004-07-02 2007-06-01 Esteve Quimica, S.A. Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion.
US20060024362A1 (en) * 2004-07-29 2006-02-02 Pawan Seth Composition comprising a benzimidazole and process for its manufacture
US8541026B2 (en) 2004-09-24 2013-09-24 Abbvie Inc. Sustained release formulations of opioid and nonopioid analgesics
CN101111233A (zh) 2004-12-23 2008-01-23 兰贝克赛实验室有限公司 稳定的口服苯并咪唑组合物及其制备方法
US20060160783A1 (en) * 2004-12-30 2006-07-20 Transform Pharmaceuticals, Inc. Novel omeprazole forms and related methods
EP1845982A2 (fr) * 2005-02-02 2007-10-24 Ranbaxy Laboratories Limited Compositions de benzimidazole orales stables preparees par un procede de stratification non aqueux
US7803817B2 (en) 2005-05-11 2010-09-28 Vecta, Ltd. Composition and methods for inhibiting gastric acid secretion
US7981908B2 (en) 2005-05-11 2011-07-19 Vecta, Ltd. Compositions and methods for inhibiting gastric acid secretion
JP2009511481A (ja) * 2005-10-06 2009-03-19 オースペックス・ファーマシューティカルズ・インコーポレイテッド 増強された治療特性を持つ、胃Ｈ＋，Ｋ＋−ＡＴＰａｓｅの重水素化阻害剤
US7553857B2 (en) 2005-12-23 2009-06-30 Lek Pharmaceuticals D.D. S-omeprazole magnesium
EP2026768B1 (fr) * 2006-06-01 2018-02-28 Dexcel Pharma Technologies Ltd. Formulation pharmaceutique comprenant des unités multiples
PL2046334T3 (pl) 2006-07-25 2015-02-27 Vecta Ltd Kompozycje i sposoby hamowania wydzielania kwasów żołądkowych z wykorzystaniem pochodnych małych kwasów dikarboksylowych w połączeniu z PPI
US20090092658A1 (en) * 2007-10-05 2009-04-09 Santarus, Inc. Novel formulations of proton pump inhibitors and methods of using these formulations
EP2068841B1 (fr) 2006-10-05 2018-09-26 Santarus, Inc. Nouvelles formulations pour une libération immédiate d'inhibiteurs de pompe à protons et procédés d'utilisation de ces formulations
MX2009004475A (es) 2006-10-27 2009-08-12 Univ Missouri Composiciones que comprenden agentes acido labiles que inhiben la bomba de protones, por lo menos otro agente farmaceuticamente activo y metodos de uso de las misma.
EP1947099A1 (fr) 2007-01-18 2008-07-23 LEK Pharmaceuticals D.D. Procédé pour l'élimination de solvant des sels d'oméprazole
US8911787B2 (en) 2008-02-26 2014-12-16 Ranbaxy Laboratories Limited Stable oral benzimidazole compositions and process of preparation thereof
CA2719868A1 (fr) 2008-04-29 2009-11-05 F. Hoffmann-La Roche Ag Pyrimidinyle pyridones inhibiteurs de jnk
US20090280173A1 (en) * 2008-05-09 2009-11-12 Ishwar Chauhan Multilayer Omeprazole Tablets
WO2009137648A1 (fr) * 2008-05-09 2009-11-12 Aptapharma, Inc. Pastilles multicouches inhibant la pompe à protons
EP2147918A1 (fr) 2008-07-21 2010-01-27 LEK Pharmaceuticals D.D. Procédé de préparation de magnésium d'oméprazole S dans une forme stable
EA201100313A1 (ru) * 2008-09-09 2011-10-31 Астразенека Аб Способ доставки фармацевтической композиции пациенту, нуждающемуся в этом
WO2010122583A2 (fr) 2009-04-24 2010-10-28 Rubicon Research Private Limited Compositions pharmaceutiques orales comprenant des substances labiles en milieu acide
US20110008432A1 (en) * 2009-06-25 2011-01-13 Pozen Inc. Method for Treating a Patient in Need of Aspirin Therapy
EA201290026A1 (ru) 2009-06-25 2012-07-30 Астразенека Аб Способ лечения пациента, имеющего риск развития язвы, связанной с приемом нестероидных противовоспалительных средств (nsaid)
WO2011080500A2 (fr) 2009-12-29 2011-07-07 Orexo Ab Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique
EP2519229A2 (fr) 2009-12-29 2012-11-07 Novartis AG Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique
WO2011080502A2 (fr) 2009-12-29 2011-07-07 Orexo Ab Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique
EP2345408A3 (fr) 2010-01-08 2012-02-29 Dr. Reddy's Laboratories Ltd. Formulations de médicament labiles acides
EP2601947A1 (fr) 2011-12-05 2013-06-12 Abo Bakr Mohammed Ali Al-Mehdar Combinaison à dose fixe pour le traitement de maladies associées à Hélicobacter pylori
CN104519888A (zh) 2011-12-28 2015-04-15 波曾公司 用于递送奥美拉唑和乙酰水杨酸的改良组合物和方法
CN102993184A (zh) * 2013-01-08 2013-03-27 湖南方盛制药股份有限公司 一种埃索美拉唑及其镁盐三水合物的制备方法
WO2016174664A1 (fr) 2015-04-29 2016-11-03 Dexcel Pharma Technologies Ltd. Compositions à désintégration par voie orale
WO2017145146A1 (fr) 2016-02-25 2017-08-31 Dexcel Pharma Technologies Ltd. Compositions comprenant des inhibiteurs de la pompe à protons
US10076494B2 (en) 2016-06-16 2018-09-18 Dexcel Pharma Technologies Ltd. Stable orally disintegrating pharmaceutical compositions
EP4598528A1 (fr) 2022-10-04 2025-08-13 Arsenil Zabirnyk Inhibition de calcification de valve aortique

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE7804231L (sv) * 1978-04-14 1979-10-15 Haessle Ab Magsyrasekretionsmedel
SE8301182D0 (sv) * 1983-03-04 1983-03-04 Haessle Ab Novel compounds
GB2189698A (en) * 1986-04-30 1987-11-04 Haessle Ab Coated omeprazole tablets
DE4035455A1 (de) * 1990-11-08 1992-05-14 Byk Gulden Lomberg Chem Fab Enantiomerentrennung
SE9302396D0 (sv) * 1993-07-09 1993-07-09 Ab Astra A novel compound form

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9501977A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1801110A1 (fr) 2005-12-22 2007-06-27 KRKA, tovarna zdravil, d.d., Novo mesto Sel d'arginine d'ésoméprazole

Also Published As

Publication number Publication date
YU49193B (sh) 2004-09-03
MA23257A1 (fr) 1995-04-01
SK2296A3 (en) 1996-10-02
SK281230B6 (sk) 2001-01-18
HUT75314A (en) 1997-05-28
ZA944933B (en) 1995-02-20
EP0707580B1 (fr) 2002-01-30
IS4186A (is) 1995-01-10
MX9405217A (es) 1995-01-31
DK0707580T3 (da) 2002-04-15
NO960068L (no) 1996-01-05
ES2100136T1 (es) 1997-06-16
AU679766B2 (en) 1997-07-10
IL110190A0 (en) 1994-10-21
US5900424A (en) 1999-05-04
NO308702B1 (no) 2000-10-16
CN1064680C (zh) 2001-04-18
JPH08512315A (ja) 1996-12-24
HK1008329A1 (en) 1999-05-07
PL175999B1 (pl) 1999-03-31
UA43343C2 (uk) 2001-12-17
KR100353783B1 (ko) 2004-04-03
GR970300015T1 (en) 1997-05-31
JP3878826B2 (ja) 2007-02-07
DZ1792A1 (fr) 2002-02-17
AU7198194A (en) 1995-02-06
FI114154B (fi) 2004-08-31
DE707580T1 (de) 1997-09-04
CZ288933B6 (cs) 2001-09-12
MY113274A (en) 2002-01-31
TNSN94079A1 (fr) 1995-04-25
SA94150058B1 (ar) 2006-06-20
YU43694A (sh) 1997-07-31
PL312440A1 (en) 1996-04-29
EG21437A (en) 2001-10-31
HRP940385A2 (en) 1997-02-28
SE9302396D0 (sv) 1993-07-09
SI0707580T1 (en) 2002-06-30
ES2100136T3 (es) 2002-09-01
EP1164132A3 (fr) 2002-01-02
DE69429774T2 (de) 2002-11-14
HU226861B1 (en) 2009-12-28
TW504509B (en) 2002-10-01
CN1126993A (zh) 1996-07-17
CA2166794C (fr) 1997-03-04
IL110190A (en) 2000-07-26
FI960101A0 (fi) 1996-01-09
PT707580E (pt) 2002-06-28
NZ268693A (en) 1997-05-26
FI960101L (fi) 1996-01-09
NO960068D0 (no) 1996-01-05
JP2002105072A (ja) 2002-04-10
EP1164132A2 (fr) 2001-12-19
JP3635432B2 (ja) 2005-04-06
WO1995001977A1 (fr) 1995-01-19
EE03127B1 (et) 1998-10-15
SG52464A1 (en) 1998-09-28
IS2075B (is) 2005-12-15
ATE212628T1 (de) 2002-02-15
RU2139868C1 (ru) 1999-10-20
HRP940385B1 (en) 2003-06-30
CZ6996A3 (en) 1996-05-15
DE69429774D1 (de) 2002-03-14
HU9503873D0 (en) 1996-02-28
BR9406940A (pt) 1996-09-10

Similar Documents

Publication Publication Date Title
AU679766B2 (en) Magnesium omeprazole
WO1995001977A9 (fr) Omeprazole de magnesium
JP6591759B2 (ja) ナルメフェン塩酸塩二水和物
RS49597B (sr) Olanzapin dihidrat d
SA98190410B1 (ar) ملح صوديوم الأوميبرازول
JP2023553930A (ja) トレブルチニブの結晶形態、その製造方法、およびその使用
HK132695A (en) Anhdrous, crystalline sodium salt of 5-chloro-3-(2-thenoyl)-2-oxindole-1-carboxamide
AU2012287160A1 (en) A crystalline form of the sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzene sulfonamide
BR112014001530B1 (pt) Formas polimórficas do sal de sódio de 4-terc-butiln-[4-cloro-2-(1-óxi-piridina-4-carbonil)- fenil]-benzeno sulfonamida, composição farmacêutica e método de produção da mesma
MXPA03003761A (es) Formas de cristales y solvatos de clorhidrato de ondansetron y procesos para su preparacion.
JPS59148789A (ja) 高度に結晶性のナトリウムセフオペラゾンの製法
US4279914A (en) Thrombocyte aggregation inhibiting composition and methods
HK1008329B (en) Magnesium omeprazole
RS53777B1 (sr) Anhidrid 8-hlor-3-pentil-3,7-dihidro-1h-purin-2,6-dion 2-amino-2-(hidroksimetil)-1,3-propandiola za lečenje bolesti
JPS63264549A (ja) 乳酸カルシウム‐グリセロール付加物およびその製法
US4358441A (en) Nicotinic derivatives of glucosamine and related pharmaceutical compositions
JPH0359063B2 (fr)
JPH10503532A (ja) レソピトロン二塩酸塩の新規多形およびその水和形その製造方法およびそれを含有する組成物
TW200827357A (en) Improved process for the manufacture of mirtazapine
MXPA01004794A (en) Crystalline forms of 3-(2, 4-dichlorobenzyl)-2-methyl-n-(pentylsulfonyl)-3h-benzimidazole-5-carboxamide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19951229

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: LT PAYMENT 951229;SI PAYMENT 951229

RAX Requested extension states of the european patent have changed

Free format text: LT PAYMENT 951229;SI PAYMENT 951229

ITCL It: translation for ep claims filed

Representative=s name: JACOBACCI CASETTA & PERANI S.P.A.

TCAT At: translation of patent claims filed
EL Fr: translation of claims filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: BA2A

Ref document number: 2100136

Country of ref document: ES

Kind code of ref document: T1

DET De: translation of patent claims
17Q First examination report despatched

Effective date: 19980710

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: ASTRAZENECA AB

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: LT PAYMENT 19951229;SI PAYMENT 19951229

REF Corresponds to:

Ref document number: 212628

Country of ref document: AT

Date of ref document: 20020215

Kind code of ref document: T

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REF Corresponds to:

Ref document number: 69429774

Country of ref document: DE

Date of ref document: 20020314

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

ET Fr: translation filed
REG Reference to a national code

Ref country code: PT

Ref legal event code: SC4A

Free format text: AVAILABILITY OF NATIONAL TRANSLATION

Effective date: 20020405

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2100136

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: GR

Ref legal event code: EP

Ref document number: 20020401721

Country of ref document: GR

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: SI

Ref legal event code: IF

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: MC

Payment date: 20130611

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20130710

Year of fee payment: 20

Ref country code: IT

Payment date: 20130620

Year of fee payment: 20

Ref country code: GR

Payment date: 20130613

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20130626

Year of fee payment: 20

Ref country code: SE

Payment date: 20130711

Year of fee payment: 20

Ref country code: ES

Payment date: 20130628

Year of fee payment: 20

Ref country code: PT

Payment date: 20130109

Year of fee payment: 20

Ref country code: CH

Payment date: 20130712

Year of fee payment: 20

Ref country code: IE

Payment date: 20130711

Year of fee payment: 20

Ref country code: BE

Payment date: 20130712

Year of fee payment: 20

Ref country code: NL

Payment date: 20130716

Year of fee payment: 20

Ref country code: DE

Payment date: 20130703

Year of fee payment: 20

Ref country code: DK

Payment date: 20130711

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20130724

Year of fee payment: 20

Ref country code: GB

Payment date: 20130703

Year of fee payment: 20

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69429774

Country of ref document: DE

REG Reference to a national code

Ref country code: DK

Ref legal event code: EUP

Effective date: 20140708

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: NL

Ref legal event code: V4

Effective date: 20140708

Ref country code: PT

Ref legal event code: MM4A

Free format text: MAXIMUM VALIDITY LIMIT REACHED

Effective date: 20140708

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20140707

BE20 Be: patent expired

Owner name: *ASTRAZENECA A.B.

Effective date: 20140708

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK07

Ref document number: 212628

Country of ref document: AT

Kind code of ref document: T

Effective date: 20140708

REG Reference to a national code

Ref country code: IE

Ref legal event code: MK9A

REG Reference to a national code

Ref country code: SE

Ref legal event code: EUG

REG Reference to a national code

Ref country code: GR

Ref legal event code: MA

Ref document number: 20020401721

Country of ref document: GR

Effective date: 20140709

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20140708

Ref country code: DE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20140709

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20141120

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20140707

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20140716

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20140709